Hydrazine hydrate (1:1) → 3-(3,4-dimethoxyphenyl)-4,4-dimethyl-1H-pyrazol-5(4H)-one

HRID 1914232Notes

Reaction equation

HRID 1914232 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[C:12]([CH3:18])([CH3:17])[C:13](OC)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.[NH2:21][NH2:22]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:12]([CH3:18])([CH3:17])[C:13](=[O:14])[NH:21][N:22]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13910611Methyl 3-(3,4-dimethoxyphenyl)-2,2-dimethyl-3-oxopropanoate2×

Product 1

HCID 139106133-(3,4-dimethoxyphenyl)-4,4-dimethyl-1H-pyrazol-5(4H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

192 g of methyl 3-(3,4-dimethoxyphenyl)-2,2-dimethyl-3-oxopropanoate (compound D1) is dissolved in 600 ml of ethanol, 145 ml hydrazine hydrate is added and the mixture is heated under reflux for 17 h. The mixture is concentrated in vacuo, resuspended in 400 ml of ethanol and concentrated again. The solids are refluxed for 60 min in 400 ml of ethanol, cooled to RT and filtered. The product is washed with 50 ml of ethanol followed by 100 ml of diethyl ether and dried in vacuo at 50° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 17 h
  3. concentrationThe mixture is concentrated in vacuo
  4. concentrationconcentrated again
  5. temperatureThe solids are refluxed for 60 min in 400 ml of ethanol
  6. filtrationfiltered
  7. washThe product is washed with 50 ml of ethanol
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-d8d30f89eb934a40a0d34a9728f624b8
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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